This proposal describes the synthesis of the first member of a novel class of organic compounds with totally hidden functional groups. The specific objective of this project is tricyclo(8.8.8.2 to the 1st and 10th power)octacos-27-yne (1 approximately), in which a carbon-carbon triple bond is surrounded by a spherical array of methylene chains. Possible synthetic routes and intermediates are discussed in detail. Once prepared, 1 approximately, will be the object of an intensive study of its physical and chemical properties to determine the effect of such shielding. Among these will be a study of its static and dynamic H1 and C13 nmr for evidence of triple bond anisotropy and ring-pseudorotational processes. Ultraviolet and infrared spectra will also be informative regarding the ability of photons to penetrate the shell. Ion cyclotron resonance and mass spectroscopic studies will yield information about its gas phase reactivity. Several prototype pi-addition reactions will be attempted in order to measure the facility with which atoms and molecules permeate the sphere, thus serving as a gauge of the chemically effective size of such entities as solvent conjugate acids. Especially informative will be the electrochemical (polarigraphic) behavior of 1 approximately. Finally, biological testing of 1 approximately and its derivatives will be carried out to determine if 1 approximately in any way mimics the antiviral properties of other caged polycyclics such as adamantyl amine.